Ethyl Acetate → 4-(2-(2-Bromophenylamino)-3,4-dioxocyclobut-1-enylamino)-3-hydroxybenzonitrile

HRID 1743150Notes

Reaction equation

HRID 1743150 reaction equation
C(O[C:4]1[C:5](=[O:19])[C:6](=[O:18])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[OH:17])C.[Br:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].C(OC(=O)C)C>CS(C)=O>[Br:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][C:4]1[C:5](=[O:19])[C:6](=[O:18])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[OH:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 119922-BromoanilineHCID 105153373-Ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dione

Product 1

HCID 98214174-(2-(2-Bromophenylamino)-3,4-dioxocyclobut-1-enylamino)-3-hydroxybenzonitrileYield 3.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dione (0.7 g, 2.71 mmol) and 2-bromoaniline (0.47 g, 2.73 mmol) were heated in 6 ml DMSO for overnight. The reaction mixture was cooled to room temperature, and ethylacetate was added and precipitates formed. The filtrate was partitioned between ethylacetate and water. The organic layer was dried over sodium sulfate and concentrated. After Gilson HPLC, 34 mg (3%) of purified product was obtained. LC/MS (H+) 386

Workup

  1. customprecipitates
  2. customformed
  3. customThe filtrate was partitioned between ethylacetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-caed5f0d9034426683d26896d44dcb8f
Source dataset
uspto-grants-2006_03
Patent number
US07008962B2

Reaction notes

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